Public bug reported:

sudoers.d contains:

backup ALL=NOPASSWD: /usr/bin/rsync --config=/etc/rsync-backup.conf
--server --daemon .

server# su backup
server$ sudo /usr/bin/rsync --config=/etc/rsync-backup.conf --server --daemon .
[sudo] password for backup:

wtf? This setup works on all my other servers, why is it prompting for a
password here? Let's check the auth.log

Aug 11 11:35:19 server sudo: pam_unix(sudo:auth): conversation failed
Aug 11 11:35:19 server sudo: pam_unix(sudo:auth): auth could not identify 
password for [backup]

"conversation failed" means nothing to me, and backup has password-based
login disabled, so not having a password is intentional...

After lots of messing around, I *accidentally* stumbled across the fact
that /usr/bin/rsync was missing. If it weren't for this accident, I
probably never would have figured it out. Can we please have an error
message more useful than "conversation failed"? Even now that I know
what the problem was, I have no idea how that message was supposed to
help me find it...

ProblemType: Bug
DistroRelease: Ubuntu 11.04
Package: sudo 1.7.4p4-5ubuntu7.1
ProcVersionSignature: Ubuntu 3.0.0-4.5-generic 3.0.0-rc6
Uname: Linux 3.0.0-4-generic x86_64
NonfreeKernelModules: nvidia
Architecture: amd64
Date: Thu Aug 11 12:44:46 2011
EcryptfsInUse: Yes
InstallationMedia: Ubuntu 10.10 "Maverick Meerkat" - Release amd64 (20101007)
ProcEnviron:
 LANGUAGE=en_GB:en
 PATH=(custom, user)
 LANG=en_GB.UTF-8
 SHELL=/bin/bash
SourcePackage: sudo
UpgradeStatus: No upgrade log present (probably fresh install)

** Affects: sudo (Ubuntu)
     Importance: Undecided
         Status: New


** Tags: amd64 apport-bug natty

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https://bugs.launchpad.net/bugs/824477

Title:
  sudo is remakably unhelpful when the target app is missing

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